Dichloromethane → HCID 23114545, compound

HRID 2080410Notes

Reaction equation

HRID 2080410 reaction equation
ClCCl.[C:4](=O)([O:32]C1C=CC([N+]([O-])=O)=CC=1)[O:5][CH2:6][C:7]1[C:8]([CH2:23][C:24]2[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=2[F:31])=[N:9][C:10]([S:13]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)(=[O:15])=[O:14])=[CH:11][CH:12]=1.CN1CCOCC1.[CH2:50]([NH2:57])[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1>CCCCCC>[CH2:50]([NH:57][C:4](=[O:32])[O:5][CH2:6][C:7]1[C:8]([CH2:23][C:24]2[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=2[F:31])=[N:9][C:10]([S:13]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)(=[O:14])=[O:15])=[CH:11][CH:12]=1)[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7504BenzylamineHCID 79724-MethylmorpholineHCID 23114589HCID 23114589, compound

Product 1

HCID 23114545HCID 23114545, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a dichloromethane (1 ml) solution of [6-(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methylpyridin-3-yl]methyl 4-nitrophenyl carbonate (51 mg, 0.089 mmol) were added N-methylmorpholine (0.020 ml, 0.18 mmol) and benzylamine (0.012 ml, 0.11 mmol) sequentially at 0° C. The resulting mixture was stirred at room temperature for 20 hours. The reaction mixture was washed with a saturated aqueous solution of ammonium chloride. The organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The residue thus obtained was subjected to flash silica gel chromatography. The fraction obtained from the eluate of hexane:ethyl acetate=4:1 was concentrated under reduced pressure. The solid thus obtained was washed with diisopropyl ether and collected by filtration to give the title compound (33 mg, 0.060 mmol, 68%) as a white solid.

Workup

  1. washThe reaction mixture was washed with a saturated aqueous solution of ammonium chloride
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue thus obtained
  6. concentrationethyl acetate=4:1 was concentrated under reduced pressure
  7. customThe solid thus obtained
  8. washwas washed with diisopropyl ether
  9. filtrationcollected by filtration

Sources & evidence

ORD record
ord-3a82a5d0e1894de5a9dbf512ca140445
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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